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Angifi Dladla is a Poet of No Sure Place. His poetry speaks for the marginalized and explores the otherwise unmentioned dynamics of South Africa's political and social landscape. In this article I explore how this label is demonstrated within his two collections of poetry, The Girl Who Then Feared to Sleep and Lament for Kofifi Machu. More specifically, my argument engages with the evolving meanings of freedom evoked by Dladla, first in his apartheid-era poetry and, second, in that of today's post-apartheid situation. I demonstrate how the black-on-black violence of the 1980s townships caused a sense of confinement that forced Dladla within himself. Only then was he able to understand freedom and chart a way forward. Following this, the article turns toward those poems that depict contemporary South Africa. My analysis suggests that when freedom, not oppression, is the official political environment of the day, the reality for many is only continued violence and despair. To chart a way out of this bleak malaise, Dladla exhorts others to write in the style of his own poetry.